8-(Dimethylamino)-1,4-dioxaspiro[4.5]decane-8-carbonitrile → HCID 12595611, compound

HRID 1179028Notes

Reaction equation

HRID 1179028 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]1([C:13]#N)[CH2:12][CH2:11][C:6]2([O:10][CH2:9][CH2:8][O:7]2)[CH2:5][CH2:4]1>O1CCCC1.C1([Mg]Cl)C=CC=CC=1>[CH3:1][N:2]([CH3:15])[C:3]1([C:13]2[CH:11]=[CH:12][CH:3]=[CH:4][CH:5]=2)[CH2:12][CH2:11][C:6]2([O:10][CH2:9][CH2:8][O:7]2)[CH2:5][CH2:4]1

Participants

4

Reactant 1

HCID 3609778-(Dimethylamino)-1,4-dioxaspiro[4.5]decane-8-carbonitrile

Product 1

HCID 12595611HCID 12595611, compoundYield 193.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 178478979HCID 178478979, compoundSolvent

Procedure

50.0 g 8-dimethylamino-1,4-dioxa-spiro[4.5]decane-8-carbonitrile were dissolved in 400 ml analytical grade tetrahydrofuran, 216 ml of a commercially obtainable two molar solution of phenylmagnesium chloride in tetrahydrofuran were added dropwise under a nitrogen atmosphere, while cooling on an ice-bath, and the mixture was stirred overnight, while warming to room temperature. For working up, 200 ml ice-cold ammonium chloride solution (20 wt. %) were added, while stirring and cooling on an ice-bath, and after 30 minutes the phases were separated. The aqueous phase was extracted twice with 250 ml ether each time, the extracts were combined with the organic phase, the mixture was washed with 200 ml water followed by 200 ml saturated sodium chloride solution, dried over sodium sulfate and filtered and the filtrate was concentrated. 60.0 g dimethyl-(8-phenyl-1,4-dioxa-spiro[4.5]dec-8-yl)-amine were obtained.

Workup

  1. additionwere added dropwise under a nitrogen atmosphere
  2. temperaturewhile cooling on an ice-bath
  3. stirringwhile stirring
  4. temperaturecooling on an ice-bath
  5. customafter 30 minutes the phases were separated
  6. extractionThe aqueous phase was extracted twice with 250 ml ether each time
  7. washthe mixture was washed with 200 ml water
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-891cb9c99a9549d8b7b413f71b763a22
Source dataset
uspto-grants-2007_10
Patent number
US07276518B2

Reaction notes

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